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Electronic Structure Rearrangement via Nitroamine-Nitroimine Tautomerism: Obtaining Thermally Stable and

Yizhen Feng1, Yaqun Dong2, Qiangqiang Liu1

  • 1Extreme-Environment-Resistant Materials Key Laboratory of Sichuan Province, Sichuan University of Science & Engineering, 180 Xueyuan Street, Huixing Lu, Zigong, Sichuan 643000, China.

Organic Letters
|March 12, 2026
PubMed

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Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
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Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
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